Glaucatotones A−I: Guaiacane-Type Sesquiterpenoids from the Roots of Lindera Glauca with Anti-Inflammatory Activity

• DOI: 10.2139/ssrn.4619393
• Publication Date: 2023-11-01T20:06:45Z
• Authors: Xinyuan Pan; Jiayi Cai; Kaohua Liu; Jiaqi Guo; Siqi Li; Ling Wang; Lizhu Han; Kexin Zhou; Xiongyu Meng; Luping Qin; Huaqiang Li
• Keywords: Anti-inflammatory

Glaucatotones A−I, nine new guaiacane-type sesquiterpenoids, along with the reported compounds, namely (1β,5β)-1-hydroxyguaia-4(15),11(13)-dieno-12,5-lactone (10) and pseudoguaianelactone C (11), were isolated from roots of Lindera glauca. The structures absolute configurations these compounds elucidated by extensive spectroscopic analyses, single-crystal X-ray diffraction, comparison experimental calculated electronic circular dichroism (ECD) data. Structurally, glaucatotone A (1) is characterized as a dihomosesquiterpenoid an unprecedented 5/5/7/6 ring system. pair enantiomers, (±)-glaucatotone B (2), represent first rearranged norsesquiterpenoid (cyclopentylmethyl)cyclohexane skeleton. 3 defined dinorsesquiterpenoid possessing 5/7/5 4−6 are three norsesquiterpenoids, 4 5 stereoisomers. In vitro bioactivity, (−)-2 9 selectively inhibited Bcap-37 Du-145 cells IC50 values 5.6 5.5 μM, respectively. anti-inflammatory activity 1−9 tested, 1, (±)-2 7 exhibited potent inhibitory effects.